Main image of article Leveling Up: How to Go from Developer to CTO
When Meebo co-founder Elaine Wherry created her social, chat aggregator and personalized content company, she decided to keep a diary of all the mistakes she made along the way. To her surprise, she found she wasn't alone in the types of gaffes she committed when moving from individual employee to manager to a high-level muckety-muck. During a session at the Silicon Valley Code Camp, Wherry, who left Meebo earlier this year prior to its acquisition by Google, laid out some of the common challenges folks make in the migration from individual contributor to CTO. "I found the more experience I gained, the sooner I was able to identify mistakes before they happened," says Wherry.,

Worker Bee to Manager

At some point, a developer may find the boss tapping them on the shoulder, asking them to be a manager. "And you say, 'Cool, but can I still code?'" says Wherry, citing a typical response she's seen time and again. Newly minted managers think they'll put in 110 percent and pitch in by continuing to code while also taking on their new role, mistakenly thinking it will earn them respect with the team they're overseeing. It won't. "Your team will not be impressed. Instead, they'll wonder why they haven't had a one-on-one [discussion] with you for two weeks," Wherry warns, citing other frequent mistakes such as avoiding making the tough calls in an effort to be warm and fuzzy. The move from individual contributor to manager is one of the most challenging transitions in an upward career path, because typically there is no training, she notes. [youtube]

Manager to Director

Another tap on the shoulder by your boss. But this time, your migration up the proverbial corporate ladder is one that may take you outside of your comfort zone. Rather than managing just your team, you will be asked to manage other teams as well. That's when history often repeats itself. In an effort to divide and conquer, you ask someone on your team to be an impromptu manager, which morphs into a permanent situation. "There is no support for the new manager," Wherry says. Newly anointed directors need to give managers the parameters within which they can operate autonomously—neither micromanaging nor leaving subordinates to flounder— and to repeatedly emphasize the goals the team should strive for while letting the managers decide how to pursue them, Wherry advises. Directors often feel that if they could level up to a vice president title, "life would be so much better," because they would be empowered to make changes they desire, Wherry says.

Leveling Up

Ah, but once you reach the VP stage, there's no room for:
  • Excuses
  • Surprises
  • Flaws
Another major shift also occurs. "For the first time, you get to see what you've been working so hard towards and for so long," Wherry says, noting that your view of the organization becomes much clearer. Expect to spend more time meeting with people outside the organization. And when you come across that shiny new thing that you want to bring back home to the company, it's imperative to get your directors to buy into that new thing. As a vice president, you have to lay out Plans A, B and C again and stress that no matter what happens, the goal needs to be hit. "As a VP, you have one goal, and align incentives and repercussions around it," Wherry says. And if directors aren't fully buying in, one workaround is creating a new "strategy team." But in either case, the goal needs to be hit, since vice presidents are typically called into company board meetings to do presentations. A new vice president who isn't hitting his or her target can "spin" the board directors at their first dog-and-pony show, but that will only work for one meeting, Wherry warns, adding that you shouldn't expect to fool the CEO.

CEO offers C-Level Title

Another tap on the shoulder. Now, the CEO is asking you to be a CTO. Expect to spend more than half your time meeting with folks outside of the company, Wherry says. Additionally, in this role, the measurement you use to hire people vastly changes. Rather than asking yourself whether prospective vice president candidates have the skills needed to do the job, it becomes a question of whether they share the same values, she notes. And one of the reasons for this shift: "If you're dissatisfied with the outcome, it's your fault."

Video: David Spark of Spark Media Solutions

Image: Ladder to Success Extension by Bigstock